Diisopropylethylamine → N-{2-[4-(5-Isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-4-trifluoromethyl-benzamide

HRID 2266397Notes

Reaction equation

HRID 2266397 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[S:16][C:17]([CH:20]([CH3:22])[CH3:21])=[N:18][N:19]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.[CH3:32][O:33][C:34]1[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:39][C:35]=1[C:36](O)=[O:37].F[B-](F)(F)F.C(OC(C(=NOC(N(C)C)=[N+](C)C)C#N)=O)C>CN(C)C=O>[CH:20]([C:17]1[S:16][C:15]([NH:14][S:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][NH:2][C:36](=[O:37])[C:35]3[CH:39]=[CH:40][C:41]([C:43]([F:45])([F:46])[F:44])=[CH:42][C:34]=3[O:33][CH3:32])=[CH:6][CH:7]=2)(=[O:13])=[O:12])=[N:19][N:18]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 36908732-Methoxy-4-(trifluoromethyl)benzoic acidHCID 687820324-(2-Amino-ethyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide hydrochloride

Product 1

HCID 16118088N-{2-[4-(5-Isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-4-trifluoromethyl-benzamideYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.53 g 4-(2-Amino-ethyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzene sulfonamide hydrochloride were dissolved in 150 ml dimethylformamide. 8.54 ml N,N-diisopropylethylamine, 3.6 g 2-methoxy-4-(trifluoromethyl)benzoic acid and 6.44 g O-((Ethoxycarbonyl)cyanomethyleneamino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the resulting residue was purified by RP-HPLC to obtain 5.0 g N-{2-[4-(5-Isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-4-trifluoromethyl-benzamide as white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-c6c524a9f23b46dbbfd1c257cfd52a13
Source dataset
uspto-grants-2010_12
Patent number
US07858647B2

Reaction notes

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